JP5796017B2 - Cosmetic composition containing jasmonic acid compound - Google Patents

Description

  The present invention relates to a composition, in particular a cosmetic and / or dermatological composition comprising a jasmonic acid compound and a nonionic associative polyurethane / polyether polymer, and also in a method for treating human keratin Of the use of these compositions. More particularly, the composition of the present invention is intended to care for and / or make up keratin.

  In the sense of the present invention, the term “keratinous” is intended to indicate, for example, skin, mucous membranes, lips, scalp, eyelashes, eyebrows, and hair.

  EP 1 331 321 promotes skin desquamation, stimulates epidermal regeneration, resists signs of skin aging, improves skin color brightness and / or smoothes facial skin For this purpose, jasmonic acid compounds such as 3-hydroxy-2-pentylcyclopentaneacetic acid are disclosed. In FR-A-62921255, these compounds are also described for use as depigmenting agents.

  Unfortunately, the introduction of the above-described jasmonic acid compound into an aqueous cosmetic formulation can reduce the viscosity to an insignificant extent, thus inducing substantial fluidization of the composition.

  A very fluid composition is difficult to apply to keratinous materials. Such compositions run off when applied to keratin, specifically the skin. Its application to the keratinous material for which treatment is desired is inaccurate and therefore its use is relatively unattractive.

  Furthermore, the presence of jasmonic acid compounds has been found to affect the thickening ability of certain conventional gelling agents.

  An alternative solution consisting of compensating for this drop in viscosity by adding fatty alcohol and / or wax has been found to be unsatisfactory. Formulations thus obtained are generally very thick, too white, applied to keratin, specifically difficult to stretch, heavy sensation, penetration during application to the skin Gives a sense of difficulty.

  Thus, there is a need to utilize compounds that are jasmonic acid compounds but can have significant thickening, if necessary.

  There is also a need to utilize cosmetic or dermatological compositions exhibiting an appropriate viscosity that can be readily applied to keratins, particularly fluid compositions that have a high particle content and retain volatility.

European Patent Application Publication No. 1333021 French patent application No.62921255

G .. Fonnum, J. Bakke, and Fk. Hansen, Colloid Polym. Sci., 271, 380-389 (1993)

  The purpose of the present invention is precisely to satisfy these needs.

  More particularly, the present invention relates to at least one jasmonic acid compound of formula (I) and at least one nonionic associative polyurethane / polyether polymer in a physiologically acceptable medium including an aqueous medium. And a composition comprising: The composition according to the invention is in particular a cosmetic and / or pharmaceutical composition, in particular a dermatological composition.

  Surprisingly, the inventors have shown that the addition of a jasmonic acid compound to a composition comprising a nonionic associative polyurethane / polyether polymer does not significantly affect the viscosity of the composition, and therefore its It was recognized that it became possible to formulate in a form suitable for handling during application. Specifically, the viscosity of the composition does not decrease.

  In addition, this particular combination of jasmonic acid compound / nonionic associative polyurethane / polyether polymer also gives the composition of the invention a pleasant appearance and also allows a comfortable sensory feel during its application. .

  According to yet another subject of the invention, the present invention relates to a non-therapeutic treatment method for caring for or making up keratin, comprising the step of applying a composition according to the invention to said keratin. .

  Compounds derived from jasmonic acid correspond to the following formula (I):

(Where
R ₁ represents a COOR ₃ group, R ₃ represents a hydrogen atom or a C ₁ -C ₄ alkyl group optionally substituted with one or more hydroxyl groups;
R ₂ represents a saturated or unsaturated linear hydrocarbon group containing 1 to 18 carbon atoms, or a saturated or unsaturated branched or cyclic hydrocarbon group containing 3 to 18 carbon atoms. (Represent)
Moreover, it is a compound selected from the optical isomers and corresponding salts.

Preferably, R ₁ is -COOH, -COOMe, -COO-CH ₂ -CH ₃ , -COO-CH ₂ -CH (OH) -CH ₂ OH, -COOCH ₂ -CH ₂ -CH ₂ OH, or- A group selected from COOCH ₂ —CH (OH) —CH ₃ is shown. Preferentially, R ₁ represents a —COOH group.

Preferentially, R ₂ represents a saturated or unsaturated linear hydrocarbon group preferably containing 2 to 7 carbon atoms. Specifically, R ₂ can be a pentyl, pentenyl, hexyl, or heptyl group.

  According to one embodiment, the compound of formula (I) is selected from 3-hydroxy-2-[(2Z) -2-pentenyl] cyclopentaneacetic acid or 3-hydroxy-2-pentylcyclopentaneacetic acid. Preferably, compound (I) is 3-hydroxy-2-pentylcyclopentaneacetic acid, which may be in particular in the form of a sodium salt.

The salts of the compounds that can be used according to the invention are specifically alkali metal, such as sodium or potassium salts; alkaline earth metals, such as calcium, magnesium, or strontium salts; metals, such as zinc , Aluminum, manganese, or copper salts; ammonium salts of formula NH ₄ ⁺ ; quaternary ammonium salts; organic amine salts such as methylamine, dimethylamine, trimethylamine, triethylamine, ethylamine, 2-hydroxyethylamine, Bis (2-hydroxyethyl) amine, or salt of tris (2-hydroxyethyl) amine; selected from lysine or arginine salt. Preferably, a salt selected from sodium, potassium, magnesium, strontium, copper, manganese, or zinc salt is used. Preferentially, the sodium salt is used.

  The compound of formula (I) as defined above is present in the composition according to the invention in a content ranging from 0.01% to 10% by weight, preferably from 0.1% to 5% by weight, relative to the total weight of the composition. Can exist.

  The composition according to the invention comprises an associative polyurethane / polyether polymer.

  In the sense of the present invention, the term “associative polymer” is understood to mean a hydrophilic polymer capable of reversibly binding to each other or to other molecules in an aqueous medium. These chemical structures more particularly include at least one hydrophilic region and at least one hydrophobic region.

  The term “hydrophobic group” is understood to mean a group or polymer comprising a saturated or unsaturated linear or branched hydrocarbon chain. When the hydrophobic group represents a hydrocarbon group, it is at least 10 carbon atoms, preferably 10-30 carbon atoms, specifically 12-30 carbon atoms, more preferably 18-30. Contains carbon atoms. Preferentially, the hydrocarbon group is derived from a monofunctional compound.

  By way of example, the hydrophobic group can be derived from a fatty alcohol such as stearyl alcohol, dodecyl alcohol, or decyl alcohol, or a polyalkylenated fatty alcohol such as Steareth-100. It may also indicate a hydrocarbon polymer, such as polybutadiene.

  Nonionic polyurethanes / polyethers according to the invention can generally be in their chains, usually polyoxyethylenic hydrophilic blocks, aliphatic sequences only and / or cycloaliphatic and / or aromatic sequences. Includes both hydrophobic blocks.

  Preferably, these polyurethane / polyethers comprise at least two lipophilic hydrocarbon chains containing 6 to 30 carbon atoms separated by hydrophilic blocks, the hydrocarbon chains comprising pendant chains, Alternatively, it may be a chain at the end of the hydrophilic block. Specifically, it is possible to include one or more suspended chains. Further, the polymer can include hydrocarbon chains at one end of the hydrophilic block or at both ends.

  The polyurethane / polyether may be in the form of multiblocks, specifically triblocks. The hydrophobic block may be at each end of the chain (e.g. a triblock copolymer containing a hydrophilic central block) or distributed at both ends and in the chain (e.g. multiblock copolymer). . These same polymers may also be graft polymers or star polymers.

  Nonionic polyurethane / polyethers containing fatty chains may be triblock copolymers, whose hydrophilic blocks are polyoxyethylene chains containing 50 to 1000 oxyethylene groups.

  Nonionic polyurethanes / polyethers contain urethane linkages between the hydrophilic blocks and the name is derived from there.

  By extension, nonionic polyurethane / polyethers containing hydrophobic chains also include those where the hydrophilic block is attached to the hydrophobic block via other chemical bonds.

  Examples of non-ionic polyurethane / polyethers containing hydrophobic chains that can be used in the present invention include Rheolate 205® containing urea functional groups sold by Rheox, or Rheolate® It is also possible to use 208, 204 or 212 and also Acrysol RM 184®.

Moreover, the product Elfacos T210 (TM) containing C ₁₂ -C ₁₄ alkyl chains made of Akzo, and C ₁₈ alkyl chains can also be mentioned the product Elfacos T212 (TM) containing.

Also available is the product DW 1206B® from Rohm & Haas, which contains C ₂₀ alkyl chains and urethane bonds, sold in water with a solids content of 20%.

  It is also possible to use solutions or dispersions of these polymers, in particular in water or aqueous / alcoholic media. Examples of such polymers that can be named are Rheolate® 255, Rheolate® 278, and Rheolate® 244 sold by the company Rheox. The products DW 1206F and DW 1206J sold by Rohm & Haas can also be used.

  Polyurethane / polyethers that can be used according to the invention are also described in the article of G. Fonnum, J. Bakke, and Fk. Hansen, Colloid Polym. Sci. 271, 380-389 (1993). You can choose from what you have.

  According to one particular form of the invention, (i) at least one polyethylene glycol containing 150-180 mol of ethylene oxide, (ii) polyoxyethylenated stearyl alcohol containing 100 mol of ethylene oxide, and (iii) Polyurethane / polyethers obtainable by polycondensation of at least three compounds including diisocyanates are used. Such polyurethane / polyethers are sold in particular under the trade name Rheolate FX 1100® from Elementis, which includes polyethylene glycol containing 136 mol of ethylene oxide and polyoxyethylene containing 100 mol of ethylene oxide. It is a polycondensation product of stearyl alcohol and hexamethylene diisocyanate (HDI) having a weight average molecular weight of 30000 (INCI name: PEG-136 / Steareth-100 / HDI copolymer).

  According to another particular form of the invention, (i) at least one polyethylene glycol containing 150 to 180 mol of ethylene oxide, (ii) stearyl alcohol or decyl alcohol, and (iii) at least one di-acid. Polyurethane / polyethers obtainable by polycondensation of at least three compounds including isocyanates are used.

  Such polyurethane / polyethers are specifically sold by Rohm & Haas under the trade names Aculyn 46® and Aculyn 44®.

  INCI name: Aculyn 46® with PEG-150 / stearyl alcohol / SMDI copolymer is 15% by weight of 150 or 180 mol ethylene oxide in a matrix of maltodextrin (4%) and water (81%) Is a polycondensation product of polyethylene glycol, stearyl alcohol, and methylene bis (4-cyclohexyl isocyanate) (SMDI) (INCI name: PEG-150 / stearyl alcohol / SMDI copolymer).

  Aculyn 44® (PEG-150 / decyl alcohol / SMDI copolymer) is a polyethylene containing 35% by weight of 150 or 180 mol of ethylene oxide in a mixture of propylene glycol (39%) and water (26%). A polycondensation product of glycol, decyl alcohol and methylene bis (4-cyclohexyl isocyanate) (SMDI) (INCI name: PEG-150 / decyl alcohol / SMDI copolymer).

  The nonionic associative polyurethane / polyether polymer described above is 0.05 wt% to 1 wt%, preferably 0.1 wt% to 0.6 wt%, preferentially 0.1 wt% to It can be present in the composition according to the invention in a content ranging from 0.5% by weight.

  Advantageously, the jasmonic acid compound of formula (I) and the nonionic associative polyurethane / polyether polymer described above have a weight ratio of compound (I) / nonionic associative polyurethane / polyether polymer of 30-60. May preferably be present in the composition according to the invention in the range of 40-50.

Viscosity measurement protocol:
The viscosity of the composition of the present invention can be measured by any method known to those skilled in the art, particularly according to the following conventional methods. Thus, the measurement can be performed at 25 ° C. using a Contraves TV or Rheomat 180 equipped with a spindle rotating at 200 rpm. A person skilled in the art can select a spindle for measuring the viscosity from spindle M1 or M2 based on the general knowledge of the person skilled in the art so that the measurement can be performed. Addition of the jasmonic acid compound as defined above to the aqueous solution containing the terpolymer according to the present invention is less than 20%, specifically 15% or less, specifically 10% or less, relative to the viscosity of the solution containing only the polymer. It is reflected in the viscosity change.

The composition according to the invention comprises a physiologically acceptable aqueous medium. The term “physiologically acceptable medium” is intended to indicate a medium that is compatible with human keratinous and / or fibers, such as, but not limited to, skin, mucous membranes, nails, scalp, and / or hair. doing. The physiologically acceptable aqueous medium, optionally an aqueous phase,, C ₁ -C ₈ alcohol, specifically, ethanol, isopropanol, tert- butanol, n- butanol; glycerol, propylene glycol or butylene glycol, And as a mixture with one or more organic solvents such as polyol ethers, or as a non-mixture.

  The composition according to the invention can also comprise a fatty phase, which can comprise oils, gums, waxes normally used in the envisaged application fields.

  Thus, according to one embodiment, the composition according to the invention is also a fatty phase that is solid at ambient temperature (20-25 ° C.) and atmospheric pressure, and / or at ambient temperature (20-25 ° C.) and atmospheric pressure. It can comprise at least one fatty phase selected from a fatty phase that is liquid.

  Liquid fatty phases suitable for the practice of the present invention can include volatile oils, non-volatile oils, and mixtures thereof. Volatile or non-volatile oils can be hydrocarbon oils, specifically animal or plant derived oils, synthetic oils, silicone oils, fluoro oils, or mixtures thereof.

  The solid fatty phase suitable for the practice of the present invention can be selected from, for example, pasty fatty substances, gums, and mixtures thereof.

  As oils or waxes that can be used in the present invention, mineral oil (liquid petrolatum), vegetable oil (liquid fraction of shea butter, sunflower oil), animal oil (perhydrosqualene), synthetic oil (perserine oil), Mention may be made of silicone oils or waxes (cyclomethicone) and fluorine oils (perfluoropolyether), beeswax, carnauba wax or paraffin wax. Fatty alcohols and fatty acids (stearic acid) can be added to these oils.

  When the composition is an emulsion, the proportion of the fatty phase can range from 5% to 80% by weight, preferably from 5% to 50% by weight relative to the total weight of the composition. The oils, waxes, emulsifiers and coemulsifiers used in the composition in emulsion form are selected from those commonly used in the cosmetic field.

  Emulsifiers and co-emulsifiers can be present in the composition of the invention in a proportion range of 0.3% to 30% by weight, specifically 0.5% to 20% by weight relative to the total weight of the composition. .

  The emulsion according to the invention can also contain lipid vesicles.

  When the composition according to the invention is an oily solution or gel, the fatty phase can be more than 90% of the total weight of the composition.

  The composition according to the invention also comprises surfactants, emulsifiers, hydrophilic or lipophilic gelling agents, hydrophilic or lipophilic additives, preservatives, antioxidants, solvents, fragrances, fillers, UV- Assumptions such as A and / or UV-B sunscreens (organic or inorganic, soluble or insoluble), pigments, fibers, chelating agents, deodorants, colorants, and other cosmetic or pharmaceutical active agents Adjuncts common in the field to be used can be contained.

  The amounts of these various adjuvants are those commonly used in the cosmetics field and can range, for example, from 0.01% to 30% of the total weight of the composition. In general, the amount is adjusted according to the formulation to be produced. Depending on their nature, these adjuvants can be introduced into the fatty phase, aqueous phase, and / or lipid globules.

  Hydrophilic gelling agents that can be used in the present invention include carboxyvinyl polymers (carbomers), acrylic copolymers such as acrylate / alkyl acrylate copolymers, polysaccharides such as polyacrylamide, hydroxypropyl cellulose, natural rubber and clay. Examples of the lipophilic gelling agent include modified clays such as benton, metal salts of fatty acids such as aluminum stearate, and hydrophobic silica.

  The compositions of the invention can be provided in any formulation form that can be contemplated. Specifically, the composition according to the invention comprises an aqueous or aqueous / alcoholic solution; dispersion; water-in-oil, oil-in-water or complex emulsion; suspension; microcapsule or microparticle; ionic and / or Alternatively, it can have the form of an aerosol composition that also includes a non-ionic type of vesicle dispersion; or a pressurized propellant. Preferentially, the composition according to the invention may be an oil-in-water emulsion.

  The composition according to the invention comprises a hair care composition, specifically a shampoo, a hair set lotion, a treatment lotion, a hair cream or gel, a dyeing composition, specifically an oxidative dyeing composition, It can be provided in the form of a hair repair lotion, a permanent composition (specifically, a first step composition for applying a permanent), a lotion or gel to resist hair loss, or an antiparasitic shampoo.

  It also includes cleansing, protective, treatment, or care compositions for the face, hands, feet, main anatomical wrinkles, or body (e.g. day cream, night cream, makeup remover). Creams, sunscreen compositions, protective or caring body milks, after-sun milks, lotions, cleansing lotions, skin care gels or foams, or artificial sunscreen compositions); make up the body or face such as foundations Compositions for bathing; Deodorizing compositions containing, for example, bactericides; Aftershave compositions; Depilatory compositions; Compositions for combating insect bites or bites; analgesic compositions; or eczema, Can be provided in the form of a dermatological or pharmaceutical composition for treating certain skin diseases such as rosacea, psoriasis, lichen, or severe pruritus .

  When the composition according to the invention is intended for peeling type use, it is in any of the above-mentioned formulation forms, but those that are easily removed by rinsing, in particular aqueous gels or aqueous or aqueous / aqueous / It can also be provided in the form of an alcoholic solution.

  The composition according to the invention may be applied by any means that allows for a uniform distribution, in particular using a cotton wool swab, rod, brush, gauze, spatula or pad, or by spraying. Can be removed by rinsing with water or by using a neutral detergent.

  The composition according to the invention can be provided in the form of a volatile or non-volatile liquid type fluid, in the form of a paste, in the form of a normal or inverse emulsion, or in the form of an impregnated support or gel.

  In particular, the composition according to the invention can be provided in solid form, in particular in the form of a compact, powder or cast solid, or in the form of a stick.

  Compositions according to the present invention also provide care products, sunscreen or after-sun products, daily light protection care products, body products, foundations for application to the face or neck, concealer products, skin tone correction Can be in the form of a tinted cream or makeup base for facial makeup, or a body makeup composition.

  The composition according to the invention is used for the purpose of improving the general condition of the epidermis, in particular the skin, in particular for maintaining or restoring its physiological function and / or its aesthetic appearance. Can do.

  Thus, the composition according to the invention advantageously has a skin tension state to resist epidermal aging, to maintain and / or stimulate moisturization and / or to resist dry skin. To improve skin, to maintain or restore skin flexibility and elasticity, to improve the mineralization of the epidermis, to improve the vitality of the epidermis, promote the exchange between cells And can be used to resist skin cracks and the appearance of cracks.

  The composition according to the invention can be intended for cosmetic and / or dermatological applications.

  Other features and advantages of the present invention will become more apparent from the following examples given as non-limiting examples. In the text above and below, proportions are given as weight percentages unless otherwise indicated.

(Example)
(Comparative Examples 1 to 4)
Aqueous gels were produced using three associative thickening polymers (two nonionic associative polyurethane / polyether polymers according to the invention and one associative polymer outside the invention) for each polymer Gels were generated with the sodium salt of 3-hydroxy-2-pentylcyclopentaneacetic acid or in the absence of the sodium salt of 3-hydroxy-2-pentylcyclopentaneacetic acid.

  The viscosity of the resulting aqueous gel was then measured after storage for 24 hours at ambient temperature (measured at 25 ° C. using a Contraves TV equipped with an M3 spindle after spinning for 10 minutes at 200 rpm). viscosity).

  These tests show that only gels containing the nonionic associative polyurethane / polyether Rheolate FX1100 and Aculyn 44 in the presence of sodium salt of 3-hydroxy-2-pentylcyclopentaneacetic acid show no decrease in viscosity, On the other hand, gels containing Aristoflex SNC in the presence of the same active agent show about 26% viscosity reduction, and gels containing Sepigel 305 show about 50% viscosity reduction. Thus, the presence of the nonionic associative polyurethane / polyether rubber makes it possible to maintain the viscosity of the aqueous gel in the presence of the sodium salt of 3-hydroxy-2-pentylcyclopentaneacetic acid.

(Example 5)
A facial care cream having the following composition was prepared.

  The resulting composition has a thick cream appearance but dissolves during application to the skin. When the composition is applied to the face, it becomes possible to restore the brightness of the skin color.

(Example 6)
Produces a volatile sunscreen fluid.

  The resulting product is stable, can be sprayed and provides sun protection to the skin in addition to the biological activity conferred by the active agent.

Claims (14)

In a physiologically acceptable aqueous medium, a compound of formula (I):

(Where
R ₁ represents a COOR ₃ group, R ₃ represents a hydrogen atom or a C ₁ -C ₄ alkyl group optionally substituted with one or more hydroxyl groups;
R ₂ represents a saturated or unsaturated linear hydrocarbon group containing 1 to 18 carbon atoms, or a saturated or unsaturated branched or cyclic hydrocarbon group containing 3 to 18 carbon atoms. (Represent)
And its optical isomers and corresponding salts,
A composition comprising a nonionic associative polyurethane / polyether polymer.   In the compound (I), R1 is -COOH, -COOMe, -COO-CH2-CH3, -COO-CH2-CH (OH) -CH2OH, -COOCH2-CH2-CH2OH, or -COOCH2-CH (OH) 2. Composition according to claim 1, characterized in that it represents a group selected from -CH3 and R2 represents a saturated or unsaturated linear hydrocarbon group containing 2 to 6 carbon atoms .   3. The composition according to claim 1, wherein the compound (I) is 3-hydroxy-2-pentylcyclopentaneacetic acid. Compounds of the formula (I) is characterized in that present in an amount in the range of 0.01% to 10% by weight relative to the total weight of the composition, in any one of claims 1 3 The composition as described.   The nonionic associative polyurethane / polyether comprises at least two lipophilic hydrocarbon chains containing 6 to 30 carbon atoms separated by hydrophilic blocks, wherein the hydrocarbon chains are suspended chains Or a chain at the end of a hydrophilic block. 5. Composition according to any one of claims 1 to 4, characterized in that   6. Composition according to claim 5, characterized in that the nonionic associative polyurethane / polyether is in the form of a triblock.   The nonionic associative polyurethane / polyether is in the form of a triblock, and the triblock hydrophilic block is a polyoxyethylene chain containing 50 to 1000 oxyethylene groups. The composition according to claim 6.   The nonionic associative polyurethane / polyether comprises (i) at least one polyethylene glycol containing 150-180 mol ethylene oxide; and (ii) a polyoxyethylenated stearyl alcohol containing 100 mol ethylene oxide; 8. A composition according to any one of claims 1 to 7, characterized in that it can be obtained by polycondensation of at least three compounds comprising a diisocyanate).   9. Composition according to any one of the preceding claims, characterized in that the nonionic associative polyurethane / polyether is a PEG-136 / Steareth-100 / HDI copolymer.   The nonionic associative polyurethane / polyether comprises (i) at least one polyethylene glycol containing 150-180 mol ethylene oxide, (ii) stearyl alcohol or decyl alcohol, and (iii) at least one diisocyanate. 8. Composition according to any one of claims 1 to 7, characterized in that it can be obtained by polycondensation of at least three compounds, including nate.   11. Composition according to claim 10, characterized in that the nonionic associative polyurethane / polyether is a PEG-150 / stearyl alcohol / SMDI copolymer or a PEG-150 / decyl alcohol / SMDI copolymer. Said nonionic associative polyurethane / polyether polymers, characterized in that present in a content ranging from 0.05% to 1% by weight relative to the total weight of the composition, any of claims 1 to 11 A composition according to claim 1.   13. Composition according to any one of the preceding claims, characterized in that the composition is in the form of a water-in-oil emulsion. METHOD A method for non-therapeutically treating keratinous, the keratinous, comprising the step of applying a set composition as claimed in any one of claims 1 to 13.